US8969428B2 - UV-curable composition and the use thereof as a coating - Google Patents

UV-curable composition and the use thereof as a coating Download PDF

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Publication number
US8969428B2
US8969428B2 US12/866,924 US86692409A US8969428B2 US 8969428 B2 US8969428 B2 US 8969428B2 US 86692409 A US86692409 A US 86692409A US 8969428 B2 US8969428 B2 US 8969428B2
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composition
acrylate
polyester
epoxy acrylate
coating
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US12/866,924
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US20110028588A1 (en
Inventor
Siegfried Hiller
Sevastos Kavanozis
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PPG Industries Ohio Inc
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Karl Woerwag Lack und Farbenfabrik GmbH and Co KG
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Assigned to PPG INDUSTRIES OHIO, INC. reassignment PPG INDUSTRIES OHIO, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KARL WORWAG LACK-UND FARBENFABRIK GMBH & CO. KG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

Definitions

  • This disclosure relates to a UV-curable composition and its use, in particular, in a process for coating substrates, such as commercial vehicle axles, and a cured coat comprising such a composition and a substrate which has such a composition or such a coat.
  • compositions which is suitable for the coating of vehicle axles, in particular, commercial vehicle axles.
  • the composition should have good hiding power in combination with good curing and adhesive properties on a very wide range of substrates.
  • the composition should be capable of being applied by simple, conventional application methods.
  • a UV-curable composition for coating vehicle axles including at least one aliphatic epoxy acrylate and at least one acrylate selected from the group consisting of aromatic epoxy acrylate and polyester acrylate as a photochemically crosslinkable component.
  • our compositions can be cured by electromagnetic radiation, in particular, by UV radiation. It has at least one acrylate as a photochemically crosslinkable component, the acrylate being selected from the group consisting of: aromatic epoxy acrylate, aliphatic epoxy acrylate and polyester acrylate, preferably aliphatic polyester acrylate. Accordingly, the photochemically crosslinkable component may consist either of at least one aromatic epoxy acrylate or of at least one aliphatic epoxy acrylate or of at least one polyester acrylate or of any desired mixtures of these three acrylate types.
  • the composition always contains, as a photochemically crosslinkable component, at least one aliphatic epoxy acrylate and additionally either at least one aromatic epoxy acrylate or a preferably aliphatic polyester acrylate.
  • the composition contains at least one reactive diluent, preferably two or more reactive diluents, at least one photoinitiator, at least one filler and/or at least one pigment.
  • One or more auxiliary additives are also preferably present.
  • the composition comprises, as photochemically crosslinkable components, both at least one aliphatic epoxy acrylate and at least one aromatic epoxy acrylate. In these cases, preferably no polyester acrylate is present in the photochemically crosslinkable component.
  • the composition then has, as crosslinkable components, only the at least one aliphatic epoxy acrylate and the at least one aromatic epoxy acrylate.
  • the composition has, as photochemically crosslinkable components, both at least one aliphatic epoxy acrylate and at least one polyester acrylate, in particular, at least one aliphatic and/or at least one aromatic polyester acrylate.
  • no aromatic epoxy acrylate is then present in the photochemically crosslinkable component.
  • the absence of the aromatic epoxy acrylate may have the advantage that yellowing effects which occur when such aromatic components are exposed to light can be avoided.
  • the composition then has, as crosslinkable components, only the at least one aliphatic epoxy acrylate and the at least one polyester acrylate, in particular, the at least one aliphatic polyester acrylate.
  • An aromatic epoxy acrylate is to be understood as meaning, in particular, an epoxy acrylate which has one or more aromatic groups.
  • An aliphatic epoxy acrylate on the other hand should, in particular, have no aromatic radicals or groups and preferably have only C atoms which are arranged in straight or branched chains. This applies analogously to the at least one aliphatic or aromatic polyester acrylate.
  • All acrylates, in particular both the at least one aromatic epoxy acrylate and the at least one aliphatic epoxy acrylate preferably have at least two, preferably from 2 to 20, ethylenic double bonds per molecule.
  • the at least one aromatic epoxy acrylate is preferably a novolac-modified epoxy acrylate, in particular, an epoxy novolac triacrylate.
  • the latter is preferably used as a 70% strength epoxy novolac triacrylate in 2-phenoxyethyl acrylate (monomer).
  • novolac-modified epoxy acrylates is very advantageous, especially with regard to corrosion protection and to chemical resistance and condensation resistance of the composition or of coats produced therefrom.
  • the at least one aliphatic epoxy acrylate is preferably a polyester-modified epoxy acrylate, in particular, a polyester-modified epoxy diacrylate.
  • polyester-modified epoxy diacrylates proves to be useful, in particular, with regard to the adhesion and the mechanical properties (protection from stonechip) of the composition or of coats produced therefrom.
  • the polyester acrylate is preferably an aliphatic polyester acrylate, in particular, a polyester diacrylate.
  • a product which can be used is, for example, the product UVP6000 from Kromachem, Leverkusen, Germany.
  • the reactive diluents preferably chosen are those which are not volatile and can therefore be incorporated into the coat matrix.
  • the final properties of a coat can also be influenced by suitable choice of reactive diluent.
  • the composition contains a tetrahydrofurfuryl acrylate as a reactive diluent.
  • Tetrahydrofurfuryl acrylates have a very good dilution effect.
  • an improvement in the protection from stonechips is surprisingly also observed.
  • the composition can, particularly preferably, contain a 2-phenoxyethyl acrylate. This surprisingly has, inter alia, a very positive effect on the anticorrosion properties of the composition or of a cured coat comprising the composition.
  • the composition preferably has an ⁇ -hydroxyketone, in particular, 2-hydroxy-2-methyl-1-phenylpropan-1-one, as a photoinitiator.
  • the composition contains a bisacylphosphine as a photoinitiator, in particular, a bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide.
  • the photoinitiators are responsible for the free radical photopolymerization if the composition is cured with electromagnetic radiation. It was found that the use of bisacylphosphines promotes thorough curing to a very great extent. With photoinitiators based on ⁇ -hydroxyketones, nontacky and very hard surfaces can be achieved.
  • the composition preferably contains one or more auxiliary additives. These serve in particular for adjusting and stabilizing the properties of the composition and of the cured coat resulting therefrom.
  • auxiliary additives such as commercially available UV absorbers (hydroxybenzophenones, benzotriazoles, oxalanilides) and free radical scavengers, such as sterically hindered amines (HALS).
  • adhesion promoter as an auxiliary additive, preferably one based on (meth)acrylate, in particular, a phosphoric acid ester methacrylate.
  • a suitable adhesion promoter is, for example, Ebecryl® 171, a product of Cytec.
  • the composition contains at least one antifoam, in particular, based on polysiloxane, as an auxiliary additive.
  • a suitable antifoam is, for example, Tego® Twin 4000, a product of Tego.
  • one or more rheological additives may be present as an auxiliary additive in the composition.
  • a rheological additive in particular, based on silicate
  • Bentone® SD2 which is sold by Rheox.
  • Thickeners particularly inorganic thickeners, such as silica, and optionally also leveling agents may also be present as an auxiliary additive in a composition.
  • Both inorganic and organic pigments may be added as pigments to the composition.
  • Carbon black, titanium dioxide and iron oxide may be mentioned here by way of example as pigments.
  • Suitable fillers are all known corresponding additives such as, for example, silica gels, limestone powder, dolomite, barium sulfate, aluminum oxide or talc.
  • the composition is, however, particularly preferred when it contains quartz powder and/or talc as a filler.
  • pigments and fillers in the form of finely milled types having a mean particle size of ⁇ 20 ⁇ m, preferably ⁇ 10 ⁇ m, is particularly advantageous.
  • the composition may contain wetting agents and dispersants as auxiliary additives. Suitable wetting agents and dispersants are known to those skilled in the art.
  • the acrylates which form the photochemically crosslinkable component are present in the following proportions, namely:
  • compositions are distinguished in that they contain the following constituents in the following proportions:
  • the stated proportions preferably sum to 100% by weight.
  • the composition may contain a proportion of one or more solvents. However, it is preferably substantially free of solvents. Instead, the viscosity can be adjusted, for example, by addition of suitable amounts of reactive diluents.
  • the viscosity of the acrylates (present as a rule as oligomers) is preferably in the range greater than 5 Pa ⁇ s (determined by means of a rotary viscometer according to DIN EN ISO 3219).
  • the viscosity of the composition is preferably in the range from 100 mPa ⁇ s to 2000 mPa ⁇ s, values from 200 mPa ⁇ s to 1000 mPa ⁇ s being further preferred within this range.
  • the composition was developed, in particular, for the coating of vehicle axles, in particular, of commercial vehicle axles. Accordingly, the use of a composition as a coating composition, in particular, for coating substrates, such as vehicle axles, in particular, commercial vehicle axles, is also a part of this disclosure. Very generally, the possible use of the composition as a coating for assemblies in automotive construction, i.e., in particular, for engines, gears and parts thereof, should be singled out in particular.
  • a composition is applied to the substrate to be coated and is then cured.
  • Curing the composition preferably takes place under an inert gas atmosphere, but this measure is not absolutely essential.
  • curing is effected with UV radiation.
  • the substrate is, in particular, a vehicle axle, particularly preferably a commercial vehicle axle.
  • a coat provides outstanding protection from surface and edge corrosion and from stonechips. Moreover, it has continuous heat resistance up to 140° C. It adheres very well to metals, such as steel and gray cast iron, and to various primed add-on parts (synthetic resin primer, zinc, zinc or iron phosphatizing, powder coating, cathodic dip coating). Particularly in solvent-free form, curing of the composition to give a coat can be effected within a few seconds. The coat can be overcoated with conventional coats without any problems (refinishing).
  • a preferred composition has the following 17 constituents:
  • Photocryl E203/30PE from PC-Resin
  • Photocryl E207 from PC-Resin
  • Polyester-modified epoxy diacrylate 11.27
  • Sartomer 285 from Cray Valley
  • Tetrahydrofurfuryl acrylate THFA (monomer, MW 156)
  • Sartomer 399C from Cray Valley
  • 2-Phenoxyethyl acrylate PEA (monomer, MW 192) 14.25 5 Darocure 1173 (from Ciba) 2-Hydroxy-2-methyl-1-phenylpropan-1-one (MW 164.2) 3.20
  • Irgacure ® 819 from Ciba) Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide 0.80 (MW 418.5)
  • Ebecryl ® 171 from Cytec
  • the composition was formulated absolutely solvent-free. Selected reactive diluents were used for adjusting the viscosity. The chosen reactive diluents have the advantage that they are incorporated into the coat matrix and are therefore not volatile.
  • the composition according to the example has a viscosity in the range from 500 to 600 mPa ⁇ s.
  • composition can be outstandingly applied and can be very rapidly cured by UV radiation.
  • the combination of two photoinitiators ensures that the applied coat cures without problems at any desired point.
  • the composition In cured form, the composition has outstanding properties with respect to stonechip and corrosion protection properties.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
US12/866,924 2008-02-14 2009-02-12 UV-curable composition and the use thereof as a coating Active 2029-05-25 US8969428B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102008010346 2008-02-14
DE102008010346.2A DE102008010346B4 (de) 2008-02-14 2008-02-14 UV-härtbare Zusammensetzung, ihre Verwendung als Beschichtungsmittel und Verfahren zur Lackierung von Fahrzeugachsen
JP102008010346.2 2008-02-14
PCT/EP2009/000960 WO2009100899A1 (de) 2008-02-14 2009-02-12 Uv-härtbare zusammensetzung und ihre verwendung als beschichtungsmittel

Publications (2)

Publication Number Publication Date
US20110028588A1 US20110028588A1 (en) 2011-02-03
US8969428B2 true US8969428B2 (en) 2015-03-03

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US12/866,924 Active 2029-05-25 US8969428B2 (en) 2008-02-14 2009-02-12 UV-curable composition and the use thereof as a coating

Country Status (6)

Country Link
US (1) US8969428B2 (de)
EP (1) EP2242807B1 (de)
DE (1) DE102008010346B4 (de)
ES (1) ES2621453T3 (de)
PL (1) PL2242807T3 (de)
WO (1) WO2009100899A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120288707A1 (en) * 2010-01-27 2012-11-15 Central Motor Wheel Co., Ltd. Base coat coating composition, composite film, and method for producing same

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010029945A1 (de) * 2010-06-10 2011-12-15 Evonik Degussa Gmbh Neuartige Mattierungsmittel für UV-Überdrucklacke
CN103740237A (zh) * 2013-12-27 2014-04-23 上海长润发涂料有限公司 一种uv镭射辊涂哑光透明面漆
CN105199569A (zh) * 2015-10-23 2015-12-30 青岛展辰新材料有限公司 一种uv辊涂百叶窗高流平白色底漆
EP3208320B1 (de) 2016-02-19 2018-03-28 Karl Wörwag Lack- Und Farbenfabrik GmbH & Co. KG Lackzusammensetzung und ihre verwendung
CN112280440A (zh) * 2019-07-25 2021-01-29 上海飞凯光电材料股份有限公司 Uv胶涂料及其制备方法、涂装工件的制备方法
CN118480301A (zh) * 2024-06-03 2024-08-13 江苏集萃光敏电子材料研究所有限公司 一种uv固化耐高温刹车片涂料

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120288707A1 (en) * 2010-01-27 2012-11-15 Central Motor Wheel Co., Ltd. Base coat coating composition, composite film, and method for producing same
US9249309B2 (en) * 2010-01-27 2016-02-02 Fujikura Kasei Co., Ltd. Base coat coating composition, composite film, and method for producing same

Also Published As

Publication number Publication date
DE102008010346A1 (de) 2009-08-20
PL2242807T3 (pl) 2017-07-31
EP2242807B1 (de) 2017-02-01
ES2621453T3 (es) 2017-07-04
WO2009100899A1 (de) 2009-08-20
US20110028588A1 (en) 2011-02-03
EP2242807A1 (de) 2010-10-27
DE102008010346B4 (de) 2019-05-09

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